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Communication | Regular issue | Vol 53, No. 3, 2000, pp.545-548
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8812
Synthesis of (+)-Hupeol from (-)-Cytisine: Transformation of a Cyclic Imine into a Cyclic Hemiacetal

Yong-Hong Wang, Kimio Higashiyama, Hajime Kubo, Jia-Shi Li, and Shigeru Ohmiya*

*Institute of Medicinal Chemistry, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

A possible intermediate in the metabolism of lupin alkaloids, (+)-hupeol, was synthesized from (—)-cytisine by transformation of a cyclic imine into a cyclic hemiacetal by treatment with HNO2. The absolute stereochemistry of (+)-hupeol was confirmed to be 7S, 9R, which is the same as that of (—)-cytisine.